There is a lot of good information above. I had an 02 with f225's for 10 seasons which I sold last year, so I cannot comment on the HPDi's. If you have driven the boat then you probably know about its idiosyncrasies. Once you learn to trim her out right, she is a beast and can handle some rough stuff. She is a big 26ft boat with a huge cockpit thanks to the folding transom.
You will definitely want to check the saltwater washdown, livewell pumps and accompanying plumbing under the back hatch. Those pumps gave me some issues over the years because of moisture in the rear bilge and access. I had replaced all the plumbing back there a couple years back. Some owners have added hinges to the back deck plate to make access better. Once open you do have very good access to wires, hoses etc.
There are plastic inserts for the transom compartments, which always seemed to leak a little. Replacement inserts are tough to find, so be careful with them.
I would also check the side vent windows as they tend to get beaten up a little if people go back and forth to the bow a lot and they are open. The hardware is plastic and I ended up having to replace both windows and the corresponding hardware over the years.
I removed all of the striping and logos on my boat, as I preferred the cleaner look. I also replaced the blue helm enclosure with white at the same time. Replacement striping should be easy to find. New logos may need to made at a graphic shop.
In any Grady of this area(early 2000's) and probably most other boats for that matter, you will want to have the surveyor pay attention to moisture levels in the gunnels, transom, and where the hardtop is mounted. These are areas that if not maintained properly can lead to water intrusion. In vessels of this age many of the fixtures in these areas may need to be re-bedded. There have been a couple of posts here over the years discussing moisture on other models.
The macerator pump for the holding tank is located inside of the holding tank, and known to have issues. Mine worked for a few seasons then conked out. Never replaced it as I always used a pump out, and never had the desire to open the holding tank and pull it out.
You may also want to take a good look at the fuel system, including hoses and tanks. The previous poster mentioned replacing his tanks. My tanks had been in good shape, but I did replace all fuel lines and filters/housing on my boat before I sold it. I have know of a couple of other guys with 265's who have also replaced the fuel lines etc. If you have the deck plates up, then that is the time you want to do it.
Overall access is pretty good everywhere in the boat. You can pretty much get to anything buy just unscrewing a cabinet or panel. Rigging tunnels and passages are good sized and for most things they are easy to work on.
Get a good surveyor and let him do his job, thats what you pay them for. If that boat checks out OK go for it and have fun with her. There are several 265 owners on here and who have been very helpful to me over the years.
